Dimethylamine → HCID 178456586, compound

HRID 892108Notes

Reaction equation

HRID 892108 reaction equation
C([N:8]1[C:16]2[C:15]3=[N:17][C@H:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][N:14]3[C:13](=[O:27])[N:12]([CH2:28][CH2:29][CH3:30])[C:11]=2[N:10]=[C:9]1[CH2:31]Cl)C1C=CC=CC=1.[CH3:33][NH:34][CH3:35]>O1CCCC1>[CH2:20]([C@@H:18]1[CH2:19][N:14]2[C:15]([C:16]3[NH:8][C:9]([CH2:31][N:34]([CH3:35])[CH3:33])=[N:10][C:11]=3[N:12]([CH2:28][CH2:29][CH3:30])[C:13]2=[O:27])=[N:17]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 69662862HCID 69662862, compound

Product 1

HCID 178456586HCID 178456586, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

Compound 42 (60 mg, 0.134 mmol) obtained in Example 42 was dissolved in tetrahydrofuran (3 mL), to the solution was added a 2 mol/L solution of dimethylamine (200 μL, 0.401 mmol, 3.1 equivalents) in tetrahydrofuran, and the mixture was stirred with heating at 70° C. for 5.5 hours. The reaction solution was concentrated and then directly purified by silica gel column chromatography (chloroform:methanol=99:1 to 97:3), and the title compound (7 mg, 19%) was obtained in a manner similar to the method by which Compound 40 was obtained from Adduct 40a in Example 40.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customdirectly purified by silica gel column chromatography (chloroform:methanol=99:1 to 97:3)

Sources & evidence

ORD record
ord-cb96bf021ecb4160a318d81c582ad0a5
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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